Pd‐catalyzed decarboxylative [3 + 2] cycloaddition: Assembly of highly functionalized spirooxindoles bearing two quaternary centers. (2nd December 2021)

• Record Type: Journal Article
• Authors: Li, Tiantian; Zhu, Xinju; Jiang, Hui; Wang, Yanong; Zheng, Nan; Peng, Tian; Gao, Rui; Shi, Linlin; Hao, Xin‐Qi; Song, Mao‐Ping
• Is Part Of: Applied organometallic chemistry. Volume 36:Number 2(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2021-12-02
• Subjects: decarboxylative cycloaddition -- isatins -- quaternary stereocenters -- spirooxindoles -- vinyl cyclic carbonates; Organometallic chemistry -- Periodicals; Organometallic compounds -- Periodicals; 547.05
• DOI: 10.1002/aoc.6516
• Languages: English
• ISSNs: 0268-2605

Abstract

Abstract : An efficient method for the practical formation of functionalized spirooxindoles, which was accompanied by generating a sterically congested spiroketal system and bearing two quaternary stereocenters via a sequential palladium, catalyzed decarboxylative [3 + 2] cycloaddition of vinylethylene carbonates (VECs) and isatins. Importantly, the redox‐neutral catalytic system possesses the characteristics of operational convenience, good functional group tolerance, and good regioselectivity and diastereoselectivity, which enables a diastereoselective synthesis of spiroketal oxindole skeletons in an excellent yield. Abstract : An efficient method for the practical formation of functionalized spirooxindoles, which was accompanied by generating a sterically congested spiroketal system and bearing two quaternary stereocenters via a sequential palladium, catalyzed decarboxylative [3 + 2] cycloaddition of vinylethylene carbonates (VECs). This conversion is characterized by excellent reactivity and diastereoselectivity, mild reaction conditions, operational convenience, and wide substrate scope and provides an efficient and concise route to some complicated skeletons.